


Beautiful

by InkStainedWings



Series: One-Shots [14]
Category: Supernatural
Genre: Bigotry & Prejudice, Gen, Gender Exploration, Gender Identity, Happy Ending, Protective Dean Winchester, Protective Gabriel, Protective Sam Winchester, Trans Jack Kline, Trans Sam Winchester
Language: English
Status: Completed
Published: 2019-07-23
Updated: 2019-10-04
Packaged: 2020-07-12 08:01:45
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 1,652
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19942843
Author URL: https://archiveofourown.org/users/InkStainedWings/pseuds/InkStainedWings
Summary: Jack remembers something Mary told him about Sam while trying to figure out his own gender identity and decides to ask him for help.AKAPure fluff about Sam buying Jack dresses.(New Chapter: Jack faces some backlash about his new dressing choices and his friends and family support him)





	1. Chapter 1

**Author's Note:**

> Beta read by Stormsong here on AO3! Thank you so much for taking the time to look through this and help me clean it up!

“Uh... Sam? Can I uh... ask you something?” Jack murmured nervously standing in the doorway to Sam’s room in the bunker. Sam looked over at him surprised but sat down the gun he had been cleaning and nodded.

“Of course, Jack. Come on in,” he said. Jack walked in closing the door behind him, which was Sam’s first hint that this wasn’t going to be an easy conversation.

“I was reading things online... Things about gender and sexuality actually,” Jack started. Sam nodded slowly wondering where this was going.

“Mary mentioned before... that you weren’t always...” Jack seemed to be trying really hard not to offend him and Sam reached out squeezing his shoulder.

“It’s okay, Jack. Yeah. When I was born they would have called me a girl. Samantha Winchester. Turns out demon blood really boosts your testosterone levels through the roof. I can’t prove that the demon blood didn’t have anything to do with me being this way, but I really believe I would have ended up Sam no matter what. It just feels right,” Sam shrugged, watching Jack for any sign of if he was just curious or if there was more. Luckily, Jack wasn’t going to make him wait to find out.

“Was it scary? Choosing to be someone different from who your family knew? Did Dean get mad? Did you have to have surgery? It looked terrifying and painful online,” Jack blurted out in a hurry.

“Where is all this coming from, Jack? Yes, it was scary. It was part of what caused my dad and I to fight so much. He didn’t like it. Dean never got angry, but he didn’t understand at first. Why I felt I needed to change. Like I said, the demon blood messed with my biology enough that I never really needed top surgery and once I started drinking Ruby’s it really set in. It’s not so different from hormone therapy, but I definitely think I would have preferred surgery over doing what I did,” he answered all of Jack’s questions patiently. Jack’s eyes fell to his hands.

“I... I’m not certain, but I felt like... maybe... I don’t know,” Jack stuttered nervously and Sam seemed to get it.

“Rowena turned you into a dog at one point, Dean’s been a demon and you and I have both been soulless. If you think you’d like to try another gender to see if it fits you better, none of us are going to judge you, Jack. We want you to feel comfortable and happy,” Sam assured him and Jack relaxed some.

“I was wondering if we might be able to buy some dresses? Just one or two even to start,” Jack finally admitted, and Sam nodded.

“I’ll go snag Dean’s card and you can meet me by the car,” he promised giving Jack a hug.

“Even if you change your mind. It’s okay to try it and see how it goes. Sometimes you need to feel it to know if it’s right,” he added as he stood to go get ready to take Jack out shopping.

“Thank you, Sam,” Jack said, looking much less upset now.

By the time they returned back to the bunker it was late and the entire trunk and back seat of the car was full of clothes and accessories. Sam had taken Jack to get a pedicure and they had even picked out some wigs so he could try some hair styles out without committing to them. Jack’s favorite part had been when they had stopped by a makeup booth at the mall, a lady there had taught him how to contour and do all his makeup. It had made him feel so... pretty. He loved it.

Once they got all of his new things into his room, Sam told him to try something on then call him. Jack picked out a frilly baby blue dress and some white knee high stockings with little blue bows at the top. Looking at himself in the mirror Jack couldn’t stop smiling. It looked so cute. He felt so cute. It felt right. He didn’t even call Sam, instead he walked to his room and knocked not wanting to hide.

Sam looked up and grinned. “It looks good! The blue really matches your eyes and those socks were a good choice.” He told him, but Jack didn’t reply just walked over and hugged Sam as tightly as he could without hurting him.

Sam rubbed his back. “If you ever need anything, Jack, I’m here. I promise. You look beautiful,” he said softly.


	2. Chapter 2

**Summary for the Chapter:**

> Jack has stopped wearing his dresses and Sam wants to know why. 
> 
> (Mentions prejudice and bigotry but has a happy ending)

**Notes for the Chapter:**

> Poor Jack. At least he has family and friends to support him.

Something was off with Jack. Sam didn't know how he knew, but he knew. At first he had been fine to let Jack keep his secrets to himself and assured himself if Jack needed him he would let him know, but he couldn't remember the last time he saw Jack smile or wear the dresses they had bought and it seemed like he was getting quieter and quieter until finally Sam had to ask.

"Jack... I noticed you've been wearing a lot of the hand me downs Dean and I gave you before again. Do you want to go shopping for some clothes that fit better in that style?" he asked carefully his eyes trying to convey to Jack that it was okay if he changed his mind about the dresses. Sam wasn't going to be upset or judge him about it.

Jack winced and looked at his cereal and Sam started to regret mentioning it at the table even if he knew Cas and Dean wouldn't care either. Maybe he should have approached him alone instead...

"No. I... Its nothing. I'm fine Sam. Thank you." He said unconvincingly and Sam was going to let it go but Dean spoke up.

"Right, just like that bruise was from a possessed chipmunk. Jack, spit it out. I thought you were against lying?" Dean said actually setting down the sandwich that was almost unable to be called a sandwich due to the ungodly amount of bacon it contained.

Sam glared at his brother but frowned deeply at the mention of a bruise. Jack had been hurt?

"I... Fine. There's this group of teens that live here in Lebanon. Sometimes they invite me to hang out with them. Well... I guess I got excited about the dresses and-" Jack started and Dean cut him off.

"Oh fuck no. I want their names and addresses." He growled and Sam was about to remind his brother that no matter how much of an asshole the kids were they couldn't kill them but Jack spoke up.

"Hold on! No! They're my friends! They were fine with it. The girls were even teaching me about how makeup worked but the restaurant owners wouldn't let me come in and so the others said they wouldn't go in either and that in a town like this one their business wouldn't last long once word got out about how prejudiced they were. I... I didn't want them to not have fun just because of me. I tried to talk them down but they started a whole protest. The restaurant owner's son and his friends got involved and he pushed Michelle so I punched him and we all kinda got in a fight. Now none of us can go and they're having issues at school for standing up for me and I just... No matter what I do, I mess up." Jack said quiet tears beading at his cheeks and this time it was Dean who reached out to put a hand on Sam's shoulder to stop the future carnage he could see brewing in his little brother's eyes. Not like they could kill asshole humans either.

"Jack, dude, none of that is your fault. Those kids? They're not just fighting for you. They're fighting for themselves too. Everyone deserves to get to be who they are and if that asshole owner is willing to do that to you, I have no doubts he's done it to others too or would do it to others if given the chance. But, luckily for us, we have an expert in these sort of things who can deal with it." Dean said his eyes gleaming and Sam and Jack both gave him a confused look until Dean jerked his thumb back to where Gabriel was leaning against the door frame having heard the whole ordeal.

"Guess you forgot it was Uncle-Nephew bonding day huh squirt?" Gabriel said while Jack lightened a little at the sight of his uncle. Sam thought it was sweet how much Jack had clearly come to love Gabriel since their return from the apocalypse world and how nice Gabriel was to him. He'd come every Thursday to take Jack out for the day and help teach him his powers or just hang out.

"What does Dean mean by that Uncle, you won't kill them will you?" Jack asked nervously still too kind to want that even for the people who treated him so rudely.

Gabriel shook his head. "No, I promise I won't kill the dick if that's all he's done. But I have been dealing with his kind for a long long time and I'll make sure you and your friends don't need to worry about it anymore. Now how about you go pick out something pretty to wear so we can hit up that candy shop I was telling you about?" Gabriel said and Jack stood up quickly to go wash out his bowl only stopping to hug Gabriel tightly and smile at Sam and Dean before nearly sprinting off to his room to get dressed.

If that restaurant just so happened to get closed due to health code violations and replaced by a new ice cream parlor owned by some rich golden eyed man with a really dumb mustache, well... they knew nothing about it.


End file.
